I’m easily frustrated by apps, sites, and services that have thousands of hours of my behavior history, but don’t serve me well with it.

Why Won’t You TripThis?

I’ve recently started using TripIt to help manage my travel. Last night I booked flights to New York for October’s Brooklyn Beta conference, and so TripIt gets my itinerary and makes everything all tidy in one place. Then I got a follow-up email from TripIt touting that they’ve found “a great hotel for [my] trip”. Great! This is the perfect opportunity to serve up contextual suggestions based on any number of factors they have at their disposal from my (admittedly short, but still detailed) purchase and travel history.

So how does TripIt capitalize on this opportunity to go above and beyond? They suggest a hotel that costs more per night than the two roundtrip flights to NYC I just booked. Is that pricey hotel a possible sales conversion? Sure, anything’s possible. But I know enough about myself and my baseline behavior to know I’m not booking a hotel for a week at that rate. Why doesn’t TripIt?

Maybe they just need more time to learn my behavior. I like their service, so I’m willing to give them the benefit of the doubt until they know me better.

Words With Well You’re No Fun

The ugliest app I use on a regular basis is Words With Friends. But sometimes my friends have real lives and I play a game of Words With Strangers. That experience should be just as enjoyable as a game with a friend, if not potentially more enjoyable because of the element of surprise and mystery.

If time is the determining factor, Words With Friends has the keys to my metaphorical kingdom. They have (or at least have had the ability to have) a detailed record of every opponent, word, game, and score for almost four years of my gameplay. Hundreds of games. Thousands of words. Millions of points (ok, maybe not the last one…). So why does the game consistently match me up with randoms who I outpace three moves in? It isn’t about high scores or my abilities; it’s about finding good competition. It’s about having fun playing a game. And it’s actually not fun to beat someone I don’t know by 200 points.

How difficult is it to query a hypothetical database and match my request for a new game with a stranger who, at minimum, has an average score somewhere in the same neighborhood of my average score? I don’t know the technical answer to that question, but I do know that act would endear me to the app in a major way because it would create a more valuable experience for me.

So Why Does This Matter?

User Experience isn’t just about flows and human/computer interactions; it’s about feel and connections. The “how” of that database query is beyond my knowledge and skill, but the “why” seems like a natural extension of the app because it drastically improves my experience as a user and keeps me coming back for more games.

Nobody gets this perfect, because humans don’t make sense. Our tastes are not neatly defined. I legitimately enjoy listening to D’Angelo, Nickelback and Huey Lewis so… good luck with music suggestions for me, Rdio. Lo, I Am Become Enigma, Destroyer of Algorithms. Netflix or Amazon regularly suggest the most ridiculous things to me. But they’re trying. Tweaking. Spending millions of man hours and dollars to improve those algorithms by 1%, because 1% more relevant is a massive improvement.

But when I get a $500 hotel email or start a game with someone who STOP GIVING ME ALL THE TRIPLE LETTERS AND HAVE SOME SELF RESPECT, I just think these services aren’t trying. They’re abdicating the user experience to automated processes that don’t care (or at least weren’t built with care). Yes, serving up contextual, relevant content based on user behavior obviously isn’t an easy job, but if you try, it can help win hearts and minds in a way your competitors can’t or won’t.